Pyridine → 5-BROMO-N-PHENYLNICOTINAMIDE

HRID 876225노트

반응식

HRID 876225 반응식
N1C=CC=CC=1.[Br:7][C:8]1[CH:9]=[C:10]([C:14](Cl)=[O:15])[CH:11]=[N:12][CH:13]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.CN(C=O)C.O1CCCC1>[Br:7][C:8]1[CH:9]=[C:10]([C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH:11]=[N:12][CH:13]=1

참가 물질

7

반응물 3

HCID 1049PyridineHCID 6115AnilineHCID 27812235-Bromonicotinoyl chloride

생성물 1

HCID 42730445-BROMO-N-PHENYLNICOTINAMIDE

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

Under argon and at RT, 32.4 ml (400 mmol, 2 eq.) of pyridine, 2.4 g (20 mmol, 0.1 eq.) of 4-dimethylaminopyridine and, dropwise, a solution of 44.1 g (200 mmol, 1.0 eq.) of 5-bromopyridine-3-carbonyl chloride in 200 ml of DMF were added to a solution of 18.6 g (200 mmol) of aniline in 500 ml of tetrahydrofuran. After 3 h, the reaction mixture was concentrated under reduced pressure. The residue was suspended in water/dichloromethane and the solid was stirred well, washed repeatedly with water and dichloromethane and dried under reduced pressure. Yield: 35.7 g (52% of theory) After phase separation of the mother liquor, the organic phase was extracted twice with dichloromethane. The combined organic phases were dried (sodium sulphate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, dichloromethane/methanol 100:1), which gave 11.7 g (18% of theory) of Example 14A.

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. washwashed repeatedly with water and dichloromethane
  3. customdried under reduced pressure
  4. customYield: 35.7 g (52% of theory) After phase separation of the mother liquor
  5. extractionthe organic phase was extracted twice with dichloromethane
  6. dry with materialThe combined organic phases were dried (sodium sulphate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (silica gel, dichloromethane/methanol 100:1), which
  10. customgave 11.7 g (18% of theory) of Example 14A

출처 및 근거

ORD 기록
ord-13b404e1bfe7402289c7be48793cf482
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987248B2

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